Otto fischer



UNITED STATES PATENT I Grains.

or'ro FISCHER, OF MUNICH, ASSIGNOR {r FARBWERKE, VORMALS MEISTER, LUGIUS & BRUNING, OF HOOHST-ON-THE-MAIN, GERMANY.

PROCESS OF PREPARING OXYHYDRO-ETHYL CHINOLINE.

SPECIFICATION forming part of Letters Patent No. 273,498, dated March 6, 1883. Application filed September 26. 1882. (Specimens) To all whom it may concern I which Idesignate as alphachinoliue sulphonio Be it known that LOTTO FISCHER, doctor of acid, forms compact crystals, whereas the philosophy, and a citizen of the Empire of Gerother, the betachinoline sulphonic acid, crysmany, residing at Munich, Germany, have intallizesin prisms. Their behavioron beingsubvented certain new and useful Improvements mitted to the operations indicated in this apin the Preparation of Oxyhydro-Ethyl Ghinplication isthe same. The alphaoxy-chinoline oline, of which the following is a specification. crystallizes in fine achromatic needles,melting My invention consists in the preparation of at 167.8 to 168.8 Fahrenheit, (120 to 122 oxyhydro-ethyl chinoline from chinoline. centigrade.) It is identical with the chinophe- 1o Itis a fact well knownthat the basic oilsfrom nal described by Weidel and Gobenzl, (Wiener 6o coal-tar contains, besides other bases, chinoline Monatsh, 1880, p. 862.) The betaoxy-chinoliue andits homologues, which may be separated by also crystallizes in achromatic needles, but its fractional distillation, treatment with weak melting-point is 446 Fahrenheit, (230 centioxidizing agents, or by other suitable methods. grade.) ()n heating these oxychinolines with 1 It is, however, chinoline which is of interest tin and hydrochloric acid upon the water bath to me. From this base I have obtained by a for several hours, they take up four atoms of series of operations new compounds which I hydrogenandchangeintooxyhydro-chinolines.

find to be valuable medical agents. After having precipitated the tin from the di- The following is a description of my method luted solution with sulphureted hydrogen,the

20 of proceeding: My process begins with pure oXyhydro-chinolines are separated by exactly chinoline sulpho -acid, which manufacture is neutralizing the filtered liquid with soda solunot herein set forth or claimed. I convert the tion. After being washed with water the oxyhychinoline into the monosulphonic acids by the dro-chinolines are crystallized from benzole or method employed by Lubo-win, (Berichte der ether. Thealphaoxyhydro-chinolineformsbeau- 25 Deutschen Ohemischen Gesellschaft zu Berlin, tiful crystals, melting atl i fi to 151.6Fahren- 1869, p. 400,)-i. 0., by heatingit with fuming heit,(12l to 12.2 centigrade.) The betaoxyhysulphuric acid to about 212 Fahrenheit, dro-chinoline crystallizesin small scales orlong centigrade.) The mass resulting from the reacneedles. Both these compounds are distintion I treat with lime, remove the calcium sulguished fronrthe oxychinolines by not being 0 phate formed, and convert the calcium salts of volatile with watersteam. When the iso- 8o chinoline sulphonic acids contained in the someric oxyhydro-chinolines are treated with lution into the sodium salts by adding the calmethyl or ethyl iodide they yield new comculated amount of carbonate-of-soda solution. pounds according to the following equations: The carbonate of lime which has been precipi- (l H NO-l-OH I=O H NO+HL 35 tated I filter off, and evaporate the filtrate to O H NO+O H I=O H NO+HI. 8 dryness. In order to obtain oxychinoline from (alpha or betaoXyhydro-chinoline)+(methyl or the sodium salts constituting the residue, I heat ethyliodide) =(hydroiodide ofoxyhydro methyl it with from two to three times its quantity of or ethyl chinoline.) hen it is intended to caustic soda and a little water, until the so produce, forinstance,the alphaoXybydro-ethyl 4o dium compound of oxychinoline shows itself chinoline, the proceedingis the following: One 0 on the surface of the melt in form of a brown molecule ofalphaoxyhydro-chinoline is heated oil. 1 now allow the melt to cool, dissolve it upon the water bath with one molecule of in water, and exactly neutralize the solution ethyliodide until the reaction, which is viowith hydrochloric acid. Oxychinoline now 'lent at first, has come to a standstill. From 5 separates in a crystalline form, and may he the crystalline mass obtained on cooling the 5 purified by distilling it in a current of steam. hydroiodide of oxyhydro-ethyl chinoline is ex- 1 must here observe that in sulphonizing tracted by means of water, and the new base chinoline two isomeric sulphonic acids are itselfis precipitated from theaqueous solution formed. They may be separated from each of the salt by means of caustic soda. It is 50 otherbycrystallizingiromwater. Oneof them, afterward purifiedbycrystallization from ether. :00

For 'use the base is transformed into the respective salt by means of hydrochloric, sulphuric, or another acid.

As it is my intention to immediately file another application and claim for oxyhydromethyl chinoline, alluded to in this application, I respectfully request that nothing in this case may serve to intefcre with said new applicanon.

What I claim as new, and wish to secure by Letters Patent, is

1. The process of manufacturing oxyhydroethyl chinoline from pure chinoline for medical and other use, which consists in first converting the same into oxyehinoline by the wellknown process,then producingoxyhydrochin0- line by treating the oxychinoline with tin and hydrochloric acid, then converting the oxyhydro-chinoline into oxyhydro-ethyl chinoline by treatment of the isomeric oxyhydro-chinolines 20 with ethyliodide by heat in a water bath, and after the reaction the extracting of oxyhydroethyl chinoline by means of water, and precipitating said base by means of caustic soda.

2. Oxyhydro-ethyl chinoline prepared by the 2 5 process herein described or by anyother means that will produce a like result.

In testimony whereof I affix my signature in presence of two witnesses.

OTTO FISCHER. [L. 8.]

Witnesses:

EMIL HENZEL, JOSEPH W. HARPER. 

